The town of Winter Park experienced many of the social and economic impacts of the Civil War’s reconstruction era. During that time, despite African Americans gaining freedoms through multiple constitutional amendments, Jim Crow laws allowed for segregation and discrimination to occur. A vote for incorporation to make Winter Park a city failed due to a lack of voters in September of 1887, but Gus Henderson’s efforts of advocacy and activism amongst the local black community helped Hannibal Square become a part of the incorporated city of Winter Park the following October — a landmark accomplishment for what had been a small Florida frontier town to date.

Gus Henderson was born near Lake City, Florida in 1862, and grew up on his own from boyhood after the death of his mother. As a young man he became a successful salesman in New York as abut was forced to quit because he encountered discrimination from the firm’s white employees. He moved back to Florida and resided in the Hannibal Square neighborhood where he would lead the black community in a march to the vote, a historic and symbolic act for African Americans after the ratification of the 15th Amendment. Gus Henderson advocated for voting rights, education, and equal rights on behalf of Winter Park’s black residents. His efforts ensured that Hannibal Square would be included as a part of the city of Winter Park. In addition, his activist work resulted in the first African Americans to be voted into local office – Walter Simpson and Frank Israel (the only two African Americans to hold a position on Winter Park’s City Council).

In 1886 Henderson established a a general printing and publishing company in the Winter Park area and on May 31, 1889, Henderson released the first issue of The (Winter Park) Advocate, one of two black-owned newspapers in Florida and the only newspaper in Winter Park read by both white and black residents. The Advocate remained in publication for approximately twelve years. Henderson later moved to Orlando, where he remained in the newspaper business, publishing the Florida Christian Recorder.

Henderson’s legacy lives on as we continue to celebrate local African American history in Winter Park. The Hannibal Square Heritage Center was established in 2007 as a community-centered tribute and museum documenting the past, present, and future contributions of Winter Park’s historic African-American community. The museum’s director and manager, Barbara Chandler, recently (2019) ran for a spot on the city council herself, advocating for some of the same values espoused in The Advocate by Gus more than 100 years before – equal access, representation, and community-first approaches.

— Katie Groves (Class of 2021)